Palladium-Catalyzed Acylation of sp2 C-H bond: Direct Access to Ketones from Aldehydes

被引:268
作者
Jia, Xiaofei [1 ]
Zhang, Shouhui [1 ]
Wang, Wenhui [1 ]
Luo, Fang [1 ]
Cheng, Jiang [1 ,2 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325027, Peoples R China
[2] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China
基金
芬兰科学院;
关键词
DIRECT ORTHO ARYLATION; DIRECT FUNCTIONALIZATION; COUPLING REACTION; AROMATIC IMINES; ARYL BROMIDES; ACTIVATION; CARBON; HETEROCYCLES; ACIDS; PD;
D O I
10.1021/ol900934g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed direct access to ketones from aldehydes via C-H cleavage of arenes is described. The procedure utilizes air as a clean and free terminal oxidant.
引用
收藏
页码:3120 / 3123
页数:4
相关论文
共 93 条
[81]   Activation of C-H bonds by metal complexes [J].
Shilov, AE ;
Shul'pin, GB .
CHEMICAL REVIEWS, 1997, 97 (08) :2879-2932
[82]   Annulation of alkenyl-substituted heterocycles via rhodium-catalyzed intramolecular C-H activated coupling reactions [J].
Tan, KL ;
Bergman, RG ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (11) :2685-2686
[83]   Highly efficient and enantioselective cyclization of aromatic imines via directed C-H bond activation [J].
Thalji, RK ;
Ellman, JA ;
Bergman, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (23) :7192-7193
[84]   Annulation of aromatic imines via directed C-H activation with Wilkinson's catalyst [J].
Thalji, RK ;
Ahrendt, KA ;
Bergman, RG ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9692-9693
[85]   Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion [J].
Thu, Hung-Yat ;
Yu, Wing-Yiu ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) :9048-9049
[86]   Stereoselective cis-addition of aromatic C-H bonds to alkynes catalyzed by dinuclear palladium complexes [J].
Tsukada, N ;
Mitsuboshi, T ;
Setoguchi, H ;
Inoue, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) :12102-12103
[87]   Synthesis of 2-arylbenzoxazoles by copper-catalyzed intramolecular oxidative C-O coupling of benzanilides [J].
Ueda, Satoshi ;
Nagasawa, Hideko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6411-6413
[88]   Palladium-catalyzed reaction of 2-hydroxy-2-methylpropiophenone with aryl bromides: A unique multiple arylation via successive C-C and C-H bond cleavages [J].
Wakui, H ;
Kawasaki, S ;
Satoh, T ;
Miura, M ;
Nomura, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8658-8659
[89]   Highly selective C-H functionalization/halogenation of acetanilide [J].
Wan, Xiaobing ;
Ma, Zhongxun ;
Li, Bijie ;
Zhang, Keya ;
Cao, Shaokui ;
Zhang, Shiwei ;
Shi, Zhangjie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7416-7417
[90]   Pd(II)-catalyzed cross-coupling of sp3 C-H bonds with sp2 and sp3 boronic acids using air as the oxidant [J].
Wang, Dong-Hui ;
Wasa, Masayuki ;
Giri, Ramesh ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7190-+